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Chapter 5: Q.36 (page 205)

a) Locate the stereogenic centers in the ball-and-stick model of ezetimibe (trade name Zetia), a cholesterol-lowering drug. (b) Label each stereogenic center as R or S.

Short Answer

Expert verified

A stereogenic center is a point in a molecule in which one carbon atom is bonded to four different groups of atoms. This carbon atom is considered to be asymmetrical in nature.

By interchanging any group on the asymmetrical carbon, it leads to the formation of a stereoisomer.

Step by step solution

01

Meaning of stereogenic centers

A stereogenic center is a point in a molecule in which one carbon atom is bonded to four different groups of atoms. This carbon atom is considered to be asymmetrical in nature.

By interchanging any group on the asymmetrical carbon, it leads to the formation of a stereoisomer.

02

Stereogenic centers in ezetimibe

The structure of the ezetimibe molecule is shown below:

It has three stereocenters, as shown in the above structure.

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Most popular questions from this chapter

a. Locate all the tetrahedral stereogenic centers in discodermolide, a tumor inhibitor isolated from the Caribbean marine sponge Discodermiadissoluta.

b. Certain carbon–carbon double bonds can also be stereogenic centers. With reference to the definition in Section 5.3, explain how this can occur, and then locate the three additional stereogenic centers in discodermolide.

c. Considering all stereogenic centers, what is the maximum number of stereoisomers possible for discodermolide?

Label each compound as R or S.

a.

b.

c.

d.

a. Label the four stereogenic centres in sorbitol as R or S.

b. How are sorbitol and A related?

c. How are sorbitol and B related?

Locate the stereogenic centers in each compound.

a.

b.

Drawn are four isomeric dimethylcyclopropanes.

a. How are the compounds in each pair related (enantiomers, diastereomers, constitutional isomers): A and B; A and C; B and C; C and D?

b. Label each compound as chiral or achiral.

c. Which compounds, alone, would be optically active?

d. Which compounds have a plane of symmetry?

e. How do the boiling points of the compounds in each pair compare: A and B; B and C; C and D?

f. Which of the compounds are meso compounds?

g. Would an equal mixture of compounds C and D be optically active? What about an equal mixture of B and C?
See all solutions

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